Apart from the typical miser image, this card brings a more positive meaning when I look at it in some of my readings for people -specially a very dear friend-.

And that is the ability to protect our energy from negative sources around us: notice how the Pentacles cover his crown, heart and feet chakras. Sometimes it is very important not to let our energy and resources get totally drained by surrounding people and circumstances. This is something therapists know much about, and which everyone in contact with the public for many hours should learn.

Unless we know how to keep well ourselves, there is no way we may help others. In other words, stinginess in sometimes necessary if we want to be generous in the long run.

Four of Pentacles
This is someone who thinks money, feels money and walks money....... figuratively speaking.

He can be tight and miser, almost for himself and by himself.
He is protecting what he has, whether he has earned it by sheer hard work or inherited it from a deceased family member. But I also feel sad for this guy. With all that money he has turned his back to the city behind him - city as the symbol of life, excitement and fun times.
This card when shown in my readings, has meant (and I did tell one querent) that she was being a tight miser and she totally agreed for and explained her reasons (I was not judging her of course). Depending on the querent's situation and the question asked, this is also being prudent and guarding your investments and looking after the pennies.

Hi, I always think of the words 'certain/sure' and 'to keep' with this card.  There is a bit of risk involved but the person is pretty definite that their decision will pay off or that they already have a lot going for them already.

When I see this card I think of Scrooge